Pet-friendly holiday rentals in Fruitville

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

4.91 out of 5 average rating, 206 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.97 out of 5 average rating, 120 reviews

Sunshine House, close to Downtown

Great location! This is a family friendly home, close to downtown and beaches, with a pool, fenced yard, and a large, screened porch for lounging and having meals outside. Close to all the great things Sarasota has to offer- museums, gardens, theaters, shopping, Sarasota Bay, and beaches. The house is 1.5 miles from downtown, 10 min to St. Armands, 15 min to Lido Beach, and about 20 min Siesta Key Beach. One dog considered with a fee. Children must be supervised at all times in the pool area.

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 111 reviews

Pool house by the bay

Come stay in our beautiful, Mid-Century Modern, light drenched home just one block from the bay with a private pool. The private yard is surrounded by lush landscaping & the pool is the perfect place to cool off on hot afternoons. The house is spacious & minimally decorated with finds from our world travels. We've recently replaced the bed and the neighborhood is quiet and easy to explore on foot. Note: this is our home, so please expect a warm lived in feel in the space, not that of a hotel.

A charming cottage is nestled among lush greenery, surrounded by tall trees and palms. A gravel pathway curves gently around the property, enhancing the serene outdoor setting. Sunlight filters through the foliage, creating dappled light across the landscape.

4.96 out of 5 average rating, 169 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Guesthouse in Gillespie Park

An outdoor patio area is shown, featuring a round table with four red metal chairs. Potted plants flank the table, and string lights hang overhead, creating an inviting space. French doors lead into the interior, framed by lush greenery.

4.84 out of 5 average rating, 330 reviews

Sarasota Getaway Guest House

Fully private & not shared with others Seasonal rates commence Nov 1 2023 - April 30, 2024 Longer Term Lower Rate Rentals commence May 1, 2024 - Nov 24 (Long Term rental rates available - please contact) Enjoy the luxuries of staying in the Gillispie Park area Dog Park, Tennis, Pickleball...... Walking distance to downtown where guests can find wonderful dining, entertainment, Saturday morning Farmers Market and much more Close to beaches and Arts and Entertainment and St. Armands Circle

Cottage in Indian Beach-Sapphire Shores

The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.

4.8 out of 5 average rating, 269 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

4.88 out of 5 average rating, 293 reviews

A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

Villa in Laurel Park

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

4.93 out of 5 average rating, 114 reviews

Your Florida Vacation Home

Imagine waking up to the smell of coffee being made at your in-home coffee bar... Grabbing the bicycles, and riding the most beautiful bike trail in Sarasota that passes right by the house... slipping on your flip-flops and taking a short 10 minute drive to the beach to catch the sunset and pick out some pretty sea shells... Heading to Main St. for a dinner and night out on the town... Whatever you may be looking for, you can find it here, at Your Florida Vacation Home.

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.93 out of 5 average rating, 106 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

4.92 out of 5 average rating, 111 reviews

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

Home in Glen Oaks

Heated Pool 3bdr 2bth Close to Downtown

Freshly remodeled home as of 2021, Great for family vacation. Amazing location right in the middle of town, no more than a ten minute drive to the incredible attractions. Easy drive to the #1 beach/Siesta beach world famous for its astonishing clear waters and impeccable views. This home has a private entrance with a heated outdoor pool. We are also pet friendly/dog. Small dog only, under 15 pounds, pet fee required.

Apartment in Gillespie Park

A modern living area features a blue sofa with decorative pillows, alongside a light wooden coffee table. The open kitchen area is visible in the background, equipped with stainless steel appliances and a dining table with neutral chairs. Natural light fills the space.

4.87 out of 5 average rating, 171 reviews

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is a full service cafe.

4.83 out of 5 average rating, 300 reviews

A dining area features a light wooden table with two white chairs, surrounded by soothing mint-colored walls. A refrigerator and a compact entertainment station are visible in the background, providing space for dining and relaxation. Natural light enhances the fresh, inviting atmosphere.

Guest suite in Sarasota

Suite 10 Mins to Beach w/ Fenced in Backyard

Welcome to your private guest suite in the heart of Sarasota - just minutes from Siesta Key, St. Armands Circle, and the best beaches, shops, and dining in town. Thoughtfully designed for comfort and convenience, this studio-inspired suite is the perfect home base for your Florida getaway. Whether you’re here to soak up the sun, explore Sarasota’s vibrant culture, or simply relax, you’ll feel right at home.

Popular amenities for Fruitville pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious screened-in pool area features a bright blue pool alongside lounge chairs. Strings of lights illuminate the space as the sunset casts a warm glow. Lush greenery surrounds the area, providing a tranquil setting for relaxation and entertainment.

5 out of 5 average rating, 15 reviews

Salt Water Heated Pool|Arcade Games|Game Room

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 161 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

An open living area features a modern white sectional sofa facing a mounted flat-screen television. A large ceiling fan and natural light from windows provide a bright atmosphere. A kitchen bar with seating is visible, along with decorative artwork on the walls.

5 out of 5 average rating, 23 reviews

Modern 3 Bed 2 Bath House Backyard + Pet Friendly

5 out of 5 average rating, 4 reviews

Splish Splash Retreat | Saltwater Pool + Grill

A spacious heated pool is enclosed by a screen, surrounded by a large patio area. Sun loungers are positioned nearby, while a shaded seating area can be seen in the background. Lush greenery and trees provide a natural backdrop, creating a serene environment.

4.92 out of 5 average rating, 24 reviews

A Whale of a Good Time!

A spacious backyard area features a mini-golf course marked by small flags, inviting relaxation and play. Comfortable hanging chairs are under a stylish pergola, while a fun play structure is visible, enhancing the outdoor space designed for family-friendly enjoyment.

5 out of 5 average rating, 16 reviews

Private Oasis: Mini Golf and firepit. 2 king beds.

A bright living area features a light-colored sofa against a soft gray wall, complemented by sheer white curtains. A wooden coffee table sits in the center, with a wall-mounted TV and decorative shelves visible on one side. Natural light streams through the windows.

4.84 out of 5 average rating, 172 reviews

Home near Lido Beach

A single-story home is presented with a clean white exterior and a dark garage door. A concrete driveway leads to the entrance, where tasteful landscaping features low-maintenance plants. Bright sunlight casts shadows on the facade, highlighting the home's inviting entrance and surrounding greenery.

4.97 out of 5 average rating, 35 reviews

Retreat in the midst of Sarasota

Pet-friendly home rentals with a pool

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 74 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Apartment in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 148 reviews

Free Early chk in 1 min-Ringling Campus, DT& Airpt

4.89 out of 5 average rating, 228 reviews

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

Guesthouse in Sarasota

Supercute Beach Themed Retreat Free Parking Wi-FI

A private pool area is enclosed by a screened-in lanai, featuring clear blue water reflecting sunlight. A patio umbrella and several chairs are positioned nearby, surrounded by lush greenery, creating a relaxing outdoor space.

4.97 out of 5 average rating, 68 reviews

GARDEN VIEW HOUSE WITH A POOL

An inviting backyard showcases a pool surrounded by a concrete patio, featuring lounge chairs and a grill. Lush greenery and tropical palms create a serene environment. A shaded area with colorful seating offers a space for relaxation, enhancing the outdoor experience.

5 out of 5 average rating, 10 reviews

Tropical Oasis: Poolside Getaway

5 out of 5 average rating, 11 reviews

Condo in Sarasota

Poolhouse 1/1, 4 min from Siesta

A private heated pool is enclosed within a screened lanai, surrounded by lush greenery. The pool area features a textured stone surface and a safety railing. Sunlight filters through the overhead structure, creating a bright and inviting atmosphere.

4.85 out of 5 average rating, 134 reviews

Casa Verde Sarasota Retreat

A secluded backyard features a heated pool surrounded by lush greenery and flowering plants. Tropical palm trees and colorful potted plants enhance the tranquil atmosphere, while the tiled pool edge adds a touch of contemporary design.

4.84 out of 5 average rating, 282 reviews

Private Siesta Beach House Oasis with Heated Pool.

Private, pet-friendly home rentals

An open living area is presented, featuring a blue couch and a wooden coffee table. A dining table with four chairs sits nearby, complemented by a kitchen with white cabinetry and modern appliances. A Christmas tree adds a seasonal touch, while windows allow natural light.

4.96 out of 5 average rating, 98 reviews

2 BR House 1.6 miles from Siesta Key Beach

The kitchen features modern white cabinetry and a light countertop, complemented by stainless steel appliances. A sleek black refrigerator and a built-in microwave are visible. A window provides natural light, and pendant lighting adds warmth to the space. Counter seating is available for convenience.

4.88 out of 5 average rating, 32 reviews

3 Bed 2 Bath | Renovated Getaway Home in Sarasota!

4.92 out of 5 average rating, 26 reviews

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

Home in Arlington Park

Coastal Retreat near Siesta Key Beach and Downtown

4.96 out of 5 average rating, 28 reviews

A spacious studio layout features a comfortable queen bed draped in crisp white linens, complemented by a cozy sectional sofa. Decorative beach-themed artwork adorns the walls, while a potted plant adds a touch of greenery. A minimalist coffee table holds magazines and decorative items.

Guesthouse in Sarasota

Private/Peaceful Studio -Pet Friendly, Fenced Yard

A spacious living area is enhanced by a soft colour palette and contemporary furnishings. Two dark sofas are positioned around a light wooden coffee table, with a large TV mounted on the wall. A dining space with a table for four is visible, along with a ceiling fan and decorative lighting.

5 out of 5 average rating, 23 reviews

Sunny 3BR Oasis • Water View • Beach Gear • Siesta

An open living space features warm wooden floors and large windows that provide ample natural light. A circular dining table is surrounded by six wire chairs. A modern chandelier hangs above the table, while a comfortable chair is positioned nearby, creating an inviting gathering area.

5 out of 5 average rating, 29 reviews

Sanctuary by the Sea

5 out of 5 average rating, 17 reviews

A private entrance features a white fence and gate with the number 1825 displayed prominently. The pathway is paved with bricks and flanked by lush greenery and colorful flowers, leading to the home's inviting entrance.

Home in Gillespie Park

The Gecko Bungalow - DT Sarasota

A living area features a yellow sofa accompanied by two blue armchairs, creating a comfortable seating arrangement. A glass coffee table is centered on a textured area rug. Natural light filters through sheer curtains, and a piece of wall art adds a touch of color to the neutral walls.